


if at first you don't succeed

by starkly



Category: Marvel Cinematic Universe
Genre: Double Dating, F/M, M/M, Misunderstandings, Multi, Polyamory
Language: English
Status: Completed
Published: 2016-03-07
Updated: 2016-03-07
Packaged: 2018-05-25 05:27:55
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,633
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6182356
Author URL: https://archiveofourown.org/users/starkly/pseuds/starkly
Summary: <blockquote class="userstuff">
              <p>Tony and Pepper think Rhodey needs to get back in the dating game. What better way to support him than by offering to go on a double date? Or two. Or three.</p>
            </blockquote>





	if at first you don't succeed

**Author's Note:**

> Originally written at the request of an anon @ [fuckyeahteamironman](http://fuckyeahteamironman.tumblr.com/post/128456263845/pepper-and-tony-double-date-with-rhodey) on tumblr.

Rhodey wasn’t sure when it started, exactly. He thought after the Christmas Incident, as it had come to be called, but it could have been before then. It probably was, he just never paid attention. His love life wasn’t much of a hot topic among them, because Pepper was more polite than Tony and Tony only ever nudged him about it every now and then.

Until that unspecified time after or maybe before the Christmas Incident, when Tony’s interest suddenly increased tenfold.

“You need to date,” Tony told him, walking into the kitchen with the giant bag of Chinese takeout they’d ordered. “You’re not getting any younger.”

“Thanks,” Rhodey said dryly, setting out the plates and forks as Tony unpacked the bag.

“I mean it. You can’t be sad and alone forever.” Tony sat and ignored the dishware in favor of using a little plastic fork that had come with the takeout to eat straight from the carton of lo mein.

“I’m not sad or alone.” Rhodey parceled out an even amount of food onto his plate, ignoring the way Tony was touching all the dumplings with his fork to pick out the best one. “What brought this up?”

“Delivery girl was cute.”

“Tell me you did not get the delivery girl’s numb — ”

“Relax, she was way too young for you.” He shoved a forkful of noodles into his mouth, then looked up to see Rhodey staring pointedly at him. “I did not get her number, all right. You happy?”

“Relieved.”

“Seriously though, we need to get you out there. Clock’s a ticking.”

“You don’t have a single analogue clock in this building.”

Tony pointed his fork at Rhodey. “Stop deflecting. I’m pretty sure there’s at least one down in Accounting. You ever try online dating? I can whip up a profile or two, you can pick your favorite. Hey, J — !”

“Tony.” Before Rhodey could say anything else, however, JARVIS interrupted smoothly,

“Sir, Miss Potts is on the line.”

Pepper’s voice, always pleasant to hear, was a welcome distraction from Tony’s current fascination with his (lack of a) dating life. “Tony, the board’s really pushing for that prototype — ”

“Pep! Great timing,” Tony interrupted her, pointing his fork at the nearest speaker even though no video screens were on. “I’m trying to get Rhodey to start dating but he’s not cooperating.”

Rhodey snorted. As if Pepper would play along with this.

“Why not?” she asked, and Rhodey’s smirk vanished.

“How do you know I’m not already dating?” he protested before Pepper could get sucked into this scheme of Tony’s.

“Come on, when was your last serious relationship? With Carol? That was a hundred years ago,” Tony scoffed.

“Do you want to start dating again?” Pepper continued, talking over Tony’s tirade of how many millions of years it’s been since he’d dated.

“I don’t know, Pep,” Rhodey answered truthfully, also ignoring Tony. With the Air Force and being War Machine — Iron Patriot — back to War Machine, it was easy to forget about stuff like that.

“Double date!” she exclaimed suddenly, startling Tony into silence. “Tony and I can double date with you. I’ve even got the perfect person I can set you up with. She’s a lawyer and she restores old cars in her free time, you’ll love her.”

Rhodey gaped at Tony as if to say ‘What the hell’s going on?’, but Tony just shrugged. “You don’t have to set me up with anyone, Pepper.”

“Trust me, it’ll go great.” There was the sound of a keyboard clacking as she typed. “Are you both free next Saturday? Never mind, I’ll make you both free. Tony, call me later about that prototype drawing. Love you, bye.”

The silence echoed a moment longer after she hung up.

“That was…unexpected,” Rhodey said at last.

“Guess we’re going on a date, honeybear,” Tony said with a grin, and Rhodey rolled his eyes and stole his egg roll in retaliation.

* * *

Pepper _did_ set up a double date for the next Saturday and, surprisingly, Rhodey did go. Pepper’s lawyer friend was just as nice as advertised and Rhodey had a surprisingly good time.

Although, having Tony and Pepper there too helped a lot. It kind of felt like _they_ were the ones wooing him and lawyer friend Amber. He wasn’t sure why he expected anything different, though; they were used to dealing with the public and putting on a good show. Plus, Rhodey quietly added, they were just fun to be around.

Amber had a good time, at least, and told Rhodey to call her. Pepper looked particularly smug when he told her and Tony this.

Until a few weeks and several more dates later, when he told them it wasn’t going to work out with Amber.

Pepper frowned. “What was wrong?”

The two of them were sitting at the kitchen table of the Avengers Tower, Tony sleepily standing in front of the coffee pot.

“She was nice,” Rhodey reassured her, “but I dunno. Not what I’m looking for.”

“Well?” Pepper prompted when she realized he wasn’t going to elaborate. “What are you looking for?”

Rhodey considered the question, then shrugged.

“We’ll try again,” Tony finally piped up, appearing behind Pepper with a mug of coffee in hand.

“You don’t have to keep doing this,” Rhodey said, but Tony shook his head.

“We had fun last time, didn’t you?”

“Yeah, but — ”

Pepper leaned forward and put her hand over his on the table. “It’s no trouble, really. Let us try again.”

Rhodey deliberated in silence again for a moment, then nodded. “Okay. But no more close friends. I felt bad enough turning down Amber.”

* * *

So they went on another double date. And another. And then even more. More double dates than he ever expected to go on with his two best friends, honestly. The women that Tony and Pepper set him up with all seemed like nice, interesting people, but he’d never know for sure, because the two of them seemed to monopolize all his attention while they were out. They were fun dates, yeah, but he wasn’t sure if he’d had a good time because of his date, or because of Tony and Pepper.

So that was turning into a problem.

“Maybe we should stop doing this double date thing,” he suggested one night over pizza and Xbox.

Tony stopped shooting Rhodey on the screen and looked over at him. “What, why?”

“Well it’s not really working, don’t you think?”

“I’m having a good time. So is Pep,” Tony said plaintively, like that was all that mattered.

Rhodey gave him a look. “Isn’t the point for _me_ to have a good time?”

Tony scowled. “Why aren’t you having a good time?”

“I’m not _not_ having a good time — ”

“What.”

“But maybe you two should sit the next one out.”

“Fine, fine.” Tony pouted as he unpaused the game, but he didn’t put up any more of a fight. “You’re still going to go out with Charlize, right?”

“I still can’t believe you got me a date with Charlize Theron.”

“Anything for you, muffintop.”

* * *

So a second date with Charlize doesn’t happen, which is understandable. Still, Rhodey can’t help wondering if the date wasn’t a little…lackluster without Tony and Pepper around. Not that he’ll admit that to Tony, because he’d have to deal with him gloating for who knew how long. At least with Pepper the gloating will be minimal.

“It was just one bad date,” she said sympathetically before bringing her arm back and spiking the tennis ball into his court.

Rhodey lunged for it and missed. “It wasn’t even bad.” He wiped his forehead with the back of his hand and moved into position for the next serve. “Just felt a little like I could have done better.”

Pepper was silent, lining up her shot, then called the score. The ball went wide, and Rhodey lobbed it back easily.

“Do you think I’m losing my touch?”

“I think your touch is just fine,” she said, returning his hit with a lob of her own. Rhodey grinned at her and she blushed, visible even though the flush of exertion on her face. “You know what I mean.”

He hit the ball harder this time, watching her run for it. “I’m just saying, maybe I’m not ready to try dating again.”

“Don’t be silly.” She got to the ball just in time to return it with an off-balanced swing, making Rhodey lunge to the side for it. “Try another double date with Tony and me.”

“I don’t think that was working. Shit!” The ball flew past his racket and bounced away.

“One more try,” Pepper suggested, picking up a new ball for the next serve. “Thirty – love.”

Rhodey fell silent for the rest of the game (40-love to Pepper). As they switched sides on the court, Rhodey stopped her and nodded.

“Sure, okay. One more try.”

Pepper beamed and handed him the ball for his serve.

* * *

Rhodey showed up to the restaurant a little early for the double date; even with Pepper’s good influence, Tony still managed to make them late to things. To his surprise, however, they were already seated and it was his date, Karen, who wasn’t there yet.

“Something holding Karen up?” he asked as he sat down. The women Tony and Pepper picked were usually very punctual, which Rhodey appreciated.

“She might be late,” Tony said, not sounding particularly apologetic. Pepper shot him a glance Rhodey couldn’t decipher. “But she said to start ordering without her.”

“If you’re sure,” Rhodey said, picking up his menu and cracking it open.

But Karen never showed that evening, though Tony assured him she was very sorry she couldn’t make it. Rhodey chalked it up to bad luck and didn’t think anything of it. But he’d promised Pepper one more try, and that didn’t really count, in his opinion, so he agreed to one more double date.

(It wasn’t because he enjoyed going on these dates with them. He’d just promised Pepper.)

Except when that date didn’t show up either, he started to get suspicious. After the third no show date, there was definitely something up.

“What are you two trying to do?” he demanded before they could flee the scene of that third attempt at a ‘final’ double date.

Tony froze with his hand on the door hand of their limo. (Of course they came to the restaurant in a limo, Tony always had to go overboard even for a single dinner date.) “What are you talking about, sweetpea?”

Rhodey wasn’t dissuaded by the endearment. “There’s no way it’s just a coincidence my last three dates all suddenly had something else going on.”

Pepper shot Tony one of those glances that were becoming all too common between them lately. “James, would you like to join us back at the tower for coffee?”

“Will you tell me what the hell you’re doing then?”

Pepper nodded, though Tony looked somewhat pained. Rhodey thought about it for a moment, then nodded as well.

He took his own car back to the tower, though Tony offered him a ride, saying he’d get someone to pick up the car, but Rhodey declined, wanting some time to himself to think about this. What were they so worried about they couldn’t just tell him there? Was he really just that bad a date everyone really canceled on him?

Which made no sense, but neither did anything else he came up with. So he made himself stop thinking about it until he pulled into the Avengers Tower garage and got in the elevator up to Tony and Pepper’s penthouse.

The two of them were already there, sitting on one of the plush couches, though they both hopped to their feet when he entered. Pepper made a beeline for him while Tony headed to the bar.

“Come sit down,” Pepper said, taking him gently by the arm and leading him back to the couch. She was still dressed up from dinner, but she’d taken off her shoes and let down her hair. “Would you like something to drink?”

He shook his head, but when Tony returned he pressed a glass of whiskey into his hand anyway. Rhodey sipped at it, because Tony only had alcohol that was too good to waste.

“I just want to know what’s going on.”

“We haven’t been entirely honest with you,” she said hesitantly, at the same time Tony blurted out,

“It was Pepper’s idea.”

Rhodey looked slightly taken aback. “What was?”

“This double date thing.” Tony shrugged, taking a sip of his drink.

“We were testing the waters,” Pepper said apologetically, though Rhodey had no idea what for. “It wasn’t supposed to go so far, but we were having a good time and…”

“We canceled your last three dates. Well, no, they never even existed. So we couldn’t cancel them, exactly, we just told you they did — ”

Rhodey held up his hand before Tony could keep rambling. He had to get a word in before he got his hopes up way too far. “But _why_?”

Tony rolled his eyes. “You really need it spelled out? You’re practically a rocket scientist, Rhodes — ”

“We wanted to go on those dates with you!” Pepper interrupted him again. Tony and Rhodey both stared at her, though likely for different reasons. Rhodey was trying to figure out if she meant what he thought she meant (what he wanted her to mean).

“Go on those dates like…you wanted to date me. Both of you?”

“Of course both of us,” Tony scoffed, like it couldn’t be more obvious. Rhodey thought they might have different definitions of ‘obvious.’

“And you couldn’t just _ask_?” Rhodey said, a little incredulously. They’d gone through this whole song and dance for…for what?

Pepper at least had the decency to look slightly put out, though that might’ve been because her plan didn’t work out the way she wanted and not because she felt sorry. “We just wanted to get a feel for it. Without springing it on you all at once.”

“And then you started lying to me,” Rhodey reminded them pointedly.

Now Pepper actually did look apologetic. “It wasn’t supposed to go that far. We just…” She glanced at Tony, who raised his hands helplessly. “We were enjoying ourselves. With you. Then you wanted to stop and we panicked.”

“You could have been enjoying yourselves more if you just told me.”

“Obviously we are realizing our mistake.” Tony froze with his drink halfway to his mouth. “Wait. Are you saying you would’ve said yes?”

Rhodey barely resisted sighing. He loved them, but they were idiots sometimes. “ _How_ many double dates did I go on with you?”

“A suspiciously large amount,” Tony agreed, squinting at him like he’d just now noticed that was kind of weird. “We thought you were hoping one of the women we picked would work out.”

Rhodey shook his head. “I _was_ because I thought that’s what you wanted!”

Tony turned to Pepper. “In retrospect, this was a terrible plan, why did I ever agree with it?”

Pepper just gave him a look before turning back to Rhodey. “You’re right. We should have just told you. That being said — ” She slid a finger over the lock on her phone, bringing up her calendar. “Are you free next Friday night?”

Rhodey hesitated, setting down his whiskey on the coffee table. “Another double date?”

“Just the two of us. And you.”

“A date and a half?” Tony tried, tapping his fingers against the side of his glass in a gesture Rhodey recognized as nervousness. After all this he was _still_ nervous?

So he grinned and leaned forward, taking Tony’s hand in one of his own and Pepper’s in the other, and said, “What time do I pick you up?”


End file.
